The beautiful leading lady, who stars in, writes and directs her hit HBO network show Insecure, became the new face of the makeup brand last month, but the former YouTube star only recently felt comfortable with becoming a beauty queen.
"I wasn't a huge makeup person, I didn't know much about it, so in being seen more and learning to build more confidence, I got into it," she explained to America's Elle magazine, noting the success of her YouTube series Awkward Black Girl was a key turning point. "Because also pre-Awkward Black Girl, I was kind of finding myself and my career and didn't really have the confidence that I do now. Confidence comes from creating something and knowing what I’m supposed to be doing and feeling like I’m good at what I’m supposed to be doing (with my life)."
Joining the ranks of former CoverGirl spokeswomen, such as Queen Latifah, Janelle Monae and Brandy Norwood, is a huge honour for Issa, who credits the ladies with helping her build confidence about her looks as a younger woman.
"Seeing Queen Latifah be a CoverGirl was a moment for me of being seen," she gushed. "It felt like, 'There's this woman that I've identified with for so long, just from (Latifah's TV show) Living Single and watching her movies and I want to be like Queen Latifah when I grow up'. She has tomboy tendencies, so for that to be represented through a beauty brand was incredible.
"And (as) for Janelle, I was in college or just out of college when she became a CoverGirl and I just thought like, 'Duh, of course she should be (a CoverGirl)'. She's flawless and she's someone of my own skin tone... (It) felt like another 'I'm being seen' moment."
Issa also received another unexpected confidence boost recently that knocked her socks off - a compliment from R&B goddess Beyonce.
"She was like, 'You're beautiful, I love your work. I’m a fan'. I died," Issa recalled with a laugh.© Cover Media